As Greek enterprises and the State overwhelmingly engage in electronic business, concise management of information systems and particularly strategic planning of information infrastructure emerge as important issues. This study highlights the appraisal of alternative solutions concerning telecommunications infrastructure, as part of broader information infrastructure planning, by developing an appropriate methodology and by applying it in the case of Technical Olympic’s Virtual Private Network, currently in the planning phase. The developed methodology comprises business-oriented analysis of the technological function, Management Science decision-making methods, financial and multicriteria appraisal methods, in order to encompass all the multidimensional effects of business telecommunications needs along with investment and operational cost. The rationale behind the application of the methodology is to provide guidelines concerning the technological composition of Technical Olympic’s network. Having conducted a system’s feasibility analysis first, this study specifies business requirements for Technical Olympic, investigates a large number of alternative compilations from a technological perspective and generates a series of flexible solutions through the evaluation process. Regarding consequent stages of strategic technological planning, an additional executive decision making guide is provided to the company, in order to support decisions based on the application of the methodology and the use of the accompanying computation tools.